Last Updated November 2018. This definitive guide to the best boots for men covers ten categories, including work boots, Chelseas, chukkas and more.

Boots always seem to get more done than shoes. While shoes are busy arguing semantics in a boardroom, boots are out in the garage actually doing work. Shoes spend their weekend shanking golf balls while boots are going over, around and through every surface on Earth. Boots have long belonged to the movers and shakers of history, and dammit if they’re not going to keep going. Here are the 50 best pairs you can buy right now.

The Chelsea Boot

Chelsea boots began life in England in the mid-19th century and didn’t stray far from home until recently. The elasticized wonders were a staple of the mid-’60s mod scene and protected the feet of seemingly every British invader from John to Ringo. Recently they’ve seen a revival on many of menswear’s best dressed. The silhouette is very slim and features elastic side panels and heel pull-tabs.

Simeon Chelsea Boots by A.P.C. $275

The Ranch Boot by Taylor Stitch $348

Craftsman Boots by R.M. Williams $495

Suede Chelsea Boots by Common Projects $525

Kingsman Chelsea Boots by George Cleverley $750

The Ankle Boot

Ankle boots might be the coolest footwear ever made — which makes them that much more difficult to pull off than their closest cousins, the Chelsea boot. They’ve graced the feet of rock stars and, in doing so, complemented the tightest pants mankind has had to offer for decades. The silhouette is similar to the Chelsea boot, but the Ankle boot utilizes zippers or straps, instead of elastic panels, to ensure a secure fit around the ankle.

Chris Inside Zip Boots by Frye $230

Suede Boots by AMI $630

Jonah Boot by Lucchese $795

Jodhpur Boots by Saint Laurent $1,045

Abbott Jodhpur Boots by John Lobb $1,835

The Wingtip Boot

The wingtip, whose brogued details bring a touch of formal embellishment to casual footwear, is dressed up enough to be worn with a suit and laid back enough to end up under denim or a pair of cords. But they’re not a mullet shoe: they’ve been around long enough to look equally good in either context.

Frend Brogue Boots by Grenson $345

Jacques Brogue Boots by Mr P. $510

Stow Brogue Boots by Tricker’s $605

Felix Brogue Boots by O’Keeffe $815

Brogue Boots by Dunhill $950

The Chukka Boot

About as casual as all-leather boots get, the chukka (or desert) boot was first worn by British soldiers in Africa during World War II. Afterward, they made their way across the Atlantic, becoming a casual staple for the second half of the 20th century and still gracing the feet of stylish men in the cooler months. Clarks made the originals, but upmarket offerings only improved on the formula. They lace up just above the ankle and traditionally feature a soft crepe sole.

Desert Boots by Clarks $125

Classic Boot by Wild Bunch $225

Chukka Boot by Sanders $285

Boston Chukka Boots by To Boot New York $325

Grove Chukka Boots by John Lobb $1,465

The Hiking Boot

For the purposes of this guide, we’ve kept a respectful distance from the more technical versions of this style, but the best pairs of old-school hiking boots boast the same alpine prowess that made them popular in the first place. Sturdy soles, heel support and lace-to-toe closures mean these boots are as hardworking as they are good-looking.

M120 Scarponcino Boot by Fracap $275

Danner Light by Danner $380

Hiker by Viberg $690

Military Hiker by Feit $1,100

Brunico Boots by Berluti $2,660

The Hunting Boot

For actual hunting, you may want something more technically advanced, but the hunting boot is a staple in the Northeast and has ensconced the feet of everyone from frat boys to Nobel prize winners. The traditional style features a hand-sewn moc-toe, a lace-up closure and a durable grippy outsole.

Original L.L. Bean Boot by L.L. Bean $135

Sherman Boot by Rancourt and Co. $325

Scout Boot by Maine Mountain Moccasin $335

America Bison 5.5 “PH” by Russell Moccasin Co. $460

Maine Guide Boots by Yuketen $630

The Work Boot

Strong, long-lasting and just stylish enough to stay on your feet for most of the colder months: that’s all a work boot really needs to be. Little wonder that the design was more or less perfected half a century ago. The no-frills lace-up style protects the lower legs and feet and usually features a durable lug sole.

8085 Iron Ranger Boots by Red Wing Heritage $320

1000 Mile Evans Boots by Wolverine $400

The Robert by Nicks Handmade Boots $437

8″ Work Boot by White’s Boots $470

Virgil Boots by Visvim $1,095

The Trench Boot

Worn since World War I, the trench boot (sometimes called an army or officer boot) is a handsome staple that’s shaken its military roots and manages to look a bit more cleaned up these days than it did stomping into Flanders. Similar to the work boot, this silhouette has a lower profile that is easier to incorporate into a variety of wardrobes.

Kenton Boots by J.Crew $248

Trench Boot by Oak Street Bootmakers $426

Service Boot by Viberg $670

Coniston Boots by Crockett and Jones $725

Combat Boots by John Lofgren $820

The Cowboy Boot

Like many Americana wardrobe staples, cowboy boots are rooted in function. Pull them on, wear them hard and use them for years. There are two mains styles: traditional cowboy boots that feature a riding heel (taller and angled) and roper boots that have a shorter heel, designed to handle a day of walking. The pointed toe and tall shaft make this boot instantly recognizable.

The Johnny by Tecovas $235

Pecos Boots by Red Wing Heritage $320

Texas Gold Boots by Heritage Boot Co. $495

Rust Crazyhorse Boots by Pinto Ranch $525

Bannock Boots by Lucchese $595

The Engineer Boot

The original engineer boots were designed to protect the feet of men who fed coals into steam engines. It melded the tall pull-on style of horse riding boots with the supportive arch and sole of a work boot. A buckled ankle strap distinguishes this style from other pull-on boots.

Engineer Boot by Red Wing Heritage $400

‘1939’ 100th Anniversary Engineer Boot by Wesco $749

Engineer Boots by Flat Head $950

Buco Horsehide Engineer Boots by The Real McCoys $1,772

Engineer Boots by Role Club Learn More: Here
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While they’re perhaps not as well known as brands in other regions, the original boot companies of the Northwest catered to the forest industry, making footwear for loggers and wildland firefighters. Here are three you should know. Read the Story

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